Chester Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Chester holiday rentals

Terrace/patio
Secluded Lodge with Private Lake Minutes from St. Louis

Holiday Home in Millstadt

Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, (213)
"The home was very clean. we enjoyd the fire pit, hot tub and fishing in the lake. "
United States
Emily E.
Secluded Lodge with Private Lake Minutes from St. Louis
Dining
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Holiday Home in Bloomsdale

Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
10.0 out of 10, Exceptional, (7)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is HK$1,400
HK$2,173 total
includes taxes & fees
30 Dec - 31 Dec
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Apartment in Ste. Genevieve

Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (271)
"Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. "
United States
Elsie H.
The price is HK$1,151
HK$1,406 total
includes taxes & fees
22 Dec - 23 Dec
Beautiful Modern Loft In Wine Country!
Fridge, microwave, oven, stovetop
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Holiday Home in New Offenburg

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
10.0 out of 10, Exceptional, (5)
"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "
United States
Tim M.
The price is HK$1,167
HK$2,333 total
includes taxes & fees
29 Dec - 30 Dec
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Cabin in Ste. Genevieve

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, (58)
"Clean spacious quiet( except for the dogs barking) kitchen pans are terrible."
United States
Barb S.
The price is HK$2,101
HK$2,808 total
includes taxes & fees
21 Dec - 22 Dec
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

Cottage in Ste. Genevieve

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
2.0 star property
10.0 out of 10, Exceptional, (18)
"Great historic property!"
United States
Rhonda R.
The price is HK$875
HK$1,607 total
includes taxes & fees
21 Dec - 22 Dec
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Fridge, microwave, oven, stovetop
Farmstead home w/hot tub

Holiday Home in Marissa

Farmstead home w/hot tub
10.0 out of 10, Exceptional, (15)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is HK$1,155
HK$2,156 total
includes taxes & fees
21 Dec - 22 Dec
Farmstead home w/hot tub
Exterior detail
"Little Brick House on Main (1865)”

Holiday Home in Ste. Genevieve

"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is HK$924
HK$1,235 total
includes taxes & fees
28 Dec - 29 Dec
"Little Brick House on Main (1865)”
Interior
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Apartment in Murphysboro

Murphysboro Retreat w/ Deck Near Kinkaid Lake!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a very clean and nice apartment within a very close drive to the Kinkaid boat launch. Easy to locate and can fit a car with a boat in tow no problem. This spot was also much more quiet than the campground or RV spots nearby. They have a great porch and a grill and we didn’t bring something for it which made me sad. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Holiday Home in Ste. Genevieve

Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (136)
"I hosted my 60th Birthday with friends and family.The house was perfect!! Thank you Jenna Properties!!"
United States
Renee L.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Outdoor dining
Doves Nest Guest House<br> Tranquil & Relaxing

Holiday Home in Ste. Genevieve

Doves Nest Guest House<br> Tranquil & Relaxing
10.0 out of 10, Exceptional, (55)
"Great place to stay while visiting Ste. Gen!"
United States
Kim K.
Doves Nest Guest House<br> Tranquil & Relaxing
Exterior
Hot Tub & Creek Views: Secluded Perryville Cabin

Cabin in Perryville

Hot Tub & Creek Views: Secluded Perryville Cabin
9.8 out of 10, Exceptional, (8)
"Property was excellent house was really nice and in a great location would stay there again for sure "
United States
David R.
Hot Tub & Creek Views: Secluded Perryville Cabin
Exterior
Private Cabin with Pond on Family Farm

Cabin in Belleville

Private Cabin with Pond on Family Farm
10.0 out of 10, Exceptional, (95)
"Great place to stay. Highly recommend. "
United States
Christopher B.
Private Cabin with Pond on Family Farm
Interior
Cozy Haven Little Hidden Gem Sleeps 4

Holiday Home in Ste.Genevieve

Cozy Haven Little Hidden Gem Sleeps 4
9.8 out of 10, Exceptional, (55)
"Super cute cottage! Very clean. Quick walk to town. We thoroughly enjoyed our stay here. "
United States
Marianne A.
Cozy Haven Little Hidden Gem Sleeps 4
Property grounds
TreeLoft at BaseCamp

Cabin in Perryville

TreeLoft at BaseCamp
2.0 star property
10.0 out of 10, Exceptional, (5)
"This place is perfect if you want a private upscale experience that is immersed in natural beauty. The treehouse is luxurious and so comfortable. We loved every minute of our stay. "
United States
joel r.
TreeLoft at BaseCamp
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Cabin in Ste. Genevieve

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
10.0 out of 10, Exceptional, (5)
"Tiny house was absolutely perfect for a quick getaway or even a longer stay had everything we needed except a toaster! Owners were great on getting in touch for anything needed."
United States
Deborah J.
The price is HK$1,533
HK$1,992 total
includes taxes & fees
21 Dec - 22 Dec
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Property grounds
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Holiday Home in Ste. Genevieve

Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
10.0 out of 10, Exceptional, (175)
"Great property and enjoyed our stay! Thank you!!"
United States
Sheila D.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Outdoor spa tub
Homestead Hideaway + Hot Tub

Holiday Home in Fults

Homestead Hideaway + Hot Tub
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,011
HK$1,913 total
includes taxes & fees
5 Jan - 6 Jan 2026
Homestead Hideaway + Hot Tub
Exterior
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

Holiday Home in Ste. Genevieve

Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (78)
"Best house we've had by far for our annual trip. "
United States
Nikolay P.
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Property grounds
Sweet Farm Stay

Holiday Home in Freeburg

Sweet Farm Stay
10.0 out of 10, Exceptional, (43)
"We had a very pleasant stay"
United States
Kate
The price is HK$1,167
HK$1,402 total
includes taxes & fees
31 Dec - 1 Jan 2026
Sweet Farm Stay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Pinckeyville Inn and Suites

Pinckeyville Inn and Suites

10/10 Excellent
"Friendly staff and clean rooms"
wayne 1-night trip
Posted 4 days ago
Pinckeyville Inn and Suites

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its golf courses and parks. Make sure you have time to check out the restaurants and entertainment choices during your trip.

What are some of the best holiday rentals that Chester has to offer?

Secluded Lodge with Private Lake Minutes from St. Louis: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Popeye Museum is one of the cultural attractions. Other places in town to visit include Fort Kaskaskia and Kaskaskia Bell.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.